Use Your Career Regrets to Wake Up to Who You're Meant to Be
There is a particular ache that lives somewhere between your ribs when you think about the path not taken. The director role you didn't apply for. The business idea you tucked away. The stretch assignment you watched someone else raise their hand for, while you sat quietly and told yourself you weren't ready.
If that sounds familiar, you are not broken. You are human. And you are also sitting on some of the most powerful information you will ever have about who you truly are — and who you are still becoming.
I want to talk about boldness regrets today, because they keep coming up in my conversations with midlife women, and I think we've been misreading them entirely.
What Boldness Regrets Actually Are
Author and researcher Daniel Pink spent years studying what people regret most, surveying more than 16,000 people across 105 countries. What he found was that our regrets aren't really about the surface stuff — the career category, the education category, the family category. They run deeper than that. They cluster around four core themes, and one of them is boldness.
According to Pink's research, one of the sturdiest findings across decades of study is that we are far more likely to regret inactions than actions — and this is especially true with careers. The things we didn't do haunt us far longer than the things we tried and stumbled through.Welcome to the Jungle
That "what if I had just gone for it" feeling you carry? That's a boldness regret. And it's worth paying attention to, not stuffing back down.
Why They Hit Differently for Us
Boldness regrets have a particular weight for women in midlife, and I don't think it's an accident. We were raised to be good girls. To follow the expected path. To put in 200% without making waves, to be grateful for what we had, and above all else, to put everyone else's needs ahead of our own.
So when we find ourselves at a crossroads moment — a real one, where something inside us quietly whispers "this could change everything" — we often choose the path that's already laid out in front of us. Not because we're cowards. Because we were trained to.
The patterns are predictable, even when they're disguised as something more reasonable. Perfectionism whispers that you just need to be a little more ready. The inner critic asks who you think you are to want something more. Family guilt reminds you of everyone who's counting on you to stay exactly where you are. Financial fear wonders what happens if you take a risk and it doesn't land. These aren't character flaws — they are the very blocks that keep you from stepping into the fullest, most alive version of yourself.
Research from Stanford University School of Medicine confirms what so many of my clients already feel in their bodies — that persistent self-doubt and fear of being exposed as inadequate keeps high-achieving individuals from internalizing their own accomplishments and pursuing the opportunities they've earned. That's not a weakness. That's a deeply conditioned response. And it can be unlearned.Mentalhealthjournal
The Story of Maria
I worked with a woman I'll call Maria. She was 47 when we started working together, and she arrived carrying what felt like five years' worth of heaviness. She'd been in marketing long enough to know it wasn't right for her anymore, and long enough to have watched a healthcare administration opportunity — one she genuinely ached for — go to someone with less experience than she had.
"I convinced myself I wasn't ready," she told me. "And now I'm sitting in a job I've outgrown, dreaming about starting my own consulting business, and telling myself I'm too old to start over."
Maria wasn't describing a character flaw. She was describing a boldness regret pattern that I see in some variation in nearly every midlife woman who comes to me. The perfectionism that said she needed to be 100% ready before she raised her hand. The imposter syndrome now whispering that who is she to deserve a business of her own. The age concern that had somehow convinced her that 47 was too late for anything.
Research published in Frontiers in Psychology found that midlife women who took action on the basis of their regrets — actually moving toward the thing they wished they'd done — showed measurably better wellbeing outcomes than those who didn't. That finding matters, because it means regret isn't the problem. Staying stuck in it is.
What Maria and I did together was stop treating her regrets as a verdict and start treating them as a map. We called it the Boldness Regret Reset.
The Boldness Regret Reset: Coming Home to Her
This is a five-step process and I want to walk you through it right now, because you can start it today.
Step One: The Boldness Regret Inventory
Write down one boldness regret from your career. Just one. The first one that rises up when I ask. Don't curate it, don't justify it, just write it down.
Step Two: Pattern Identification
Now get honest with yourself. What was really underneath that choice to play it safe? Was it perfectionism whispering you weren't quite ready? Was it the inner critic quietly asking who you are to want this? Was it family guilt, financial fear, age concerns, or the relentless pressure to keep everyone else comfortable? Name it. These blocks have been standing between you and her long enough.
Step Three: The Cost Analysis
This is where things get real. What did playing it safe actually cost you? Not in the abstract, but specifically. What opportunities might have opened? What growth did you sidestep? How is this regret still shaping the trajectory of your career right now?
When Maria sat with this question, the answers were heavy and clarifying all at once. Five years in a role that drained her. A healthcare administrator position that went to someone else. A consulting dream that felt further away with each year she waited. And perhaps the one that landed hardest — she was modeling settling for her teenage daughter.
Step Four: Your Proof of Courage
Here is the part most people skip, and it's the most important. Think of at least one time when you chose courage over comfort in your career. Not a grand gesture. Maybe you asked the question everyone else was afraid to ask. Maybe you set a boundary with a difficult colleague. Maybe you raised your hand for something that scared you and did it anyway.
For Maria, her courage moments were all rooted in protection. She advocated for her team when budget cuts threatened jobs. She spoke up in leadership meetings when decisions would harm patient care. She took on a project that stretched her skills because she believed in what it was trying to accomplish.
Here's what I want you to notice about her examples, and yours. The courage was already there— it always has been . It showed up every time something mattered more than comfort or approval. That woman has never left you. She's been waiting. Research from NIH on regret and missed opportunities suggests that the key difference between regret that paralyzes and regret that propels is whether a person can still see a path forward — the presence of future possibility is what transforms regret from a wound into a catalyst. That path forward is what we build in this step. PubMed Central
Step Five: Your Bold Move
What is the smallest bold move you could make this week? Not the whole leap. Just one thing. A conversation you've been putting off. A role you've been quietly researching. A mentor you've been meaning to reach out to. Courage is already inside you. We're not building something new — we're clearing the path back to her. And it starts with one small, brave step toward who you truly are.
What Your Regrets Are Really Telling You
When Maria and I finished her reset, something shifted. She stopped seeing her boldness regrets as evidence of her cowardice and started seeing them as a very clear signal of where her authentic power lived. Every "I should have been braver" moment was pointing directly at what she valued most. Healthcare. Meaningful impact. The courage to lead. Her own voice.
Your boldness regrets are doing the same thing for you. They are pointing you directly back to her — to the highest, most authentic version of yourself that has been waiting patiently for you to find your way home.
The whisper that surfaces on Sunday evenings, or in the middle of a meeting, or at 2am when you can't sleep — that's not anxiety. That's your inner rebel, trying to get your attention. She has been patient. She is not going to stop.
You have more career ahead of you than you think. And the woman you are becoming needs the courage your younger self was quietly building all along.
With love and fierce belief in you,
Dawn LaRae
The Midlife Career Whisperer
P.S. If you've been feeling that familiar pull toward something more aligned — but you're not quite sure where the disconnect is — take my free Career Alignment Assessment. It's a beautiful starting place for getting honest with yourself about where you are and where you're truly meant to be.
I'm Dawn LaRae, The Midlife Career Whisperer™ — I help midlife women reconnect with their most authentic selves to step boldly into their careers as the fullest, most alive version of themselves.
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